Potassium Carbonate → [4-(6-Cyano-2-methyl-pyrimidin-4-yl)oxyphenyl]methanesulfonamide

HRID 1520104Notes

Reaction equation

HRID 1520104 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]#[N:10])[CH:3]=1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][S:19]([NH2:22])(=[O:21])=[O:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[C:9]([C:4]1[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19]([NH2:22])(=[O:20])=[O:21])=[CH:14][CH:13]=2)[CH:3]=1)#[N:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 581284976-Chloro-2-methylpyrimidine-4-carbonitrileHCID 67410560(4-Hydroxyphenyl)methanesulfonamide

Product 1

HCID 118093606[4-(6-Cyano-2-methyl-pyrimidin-4-yl)oxyphenyl]methanesulfonamideYield 120.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Dissolve 6-chloro-2-methylpyrimidine-4-carbonitrile (628 mg, 4.1 mmol) in DMF (15 mL) at RT under a nitrogen atmosphere. Add (4-hydroxyphenyl)methanesulfonamide (859 mg, 4.1 mmol) and potassium carbonate (1.13 g, 8.2 mmol) to the solution. Stir at ambient temperature for 3 hours. Pour the mixture into a brine solution, and extract with EtOAc. Combine the extracts; dry over magnesium sulfate; filter; and concentrate the filtrate under reduced pressure to provide the title compound (80% pure, 1.5 g, 96.4%). MS (m/z): 305 (M+1).

Workup

  1. extractionextract with EtOAc
  2. dry with materialdry over magnesium sulfate
  3. filtrationfilter
  4. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c853f3f9dca5415b9bdbcd1e05b772e3
Source dataset
uspto-grants-2015_07
Patent number
US09073901B2

Reaction notes

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